An upper-middle-class black man struggles to raise his children with a sense of cultural identity despite constant contradictions and obstacles coming from his liberal wife, old-school father and his assimilated, color-blind kids.
Advertising executive Dre happily anticipates a promotion; Andre Jr. wants to covert to Judaism and have a bar mitzvah like his friends.
When Dre decides to give Andre Jr. the sex talk, he instantly regrets it when his son won't stop asking questions.
Dre sets out to expand Andre Jr’s social circle to include more black kids after he discovers Andre Jr. is clueless about “the nod.” Meanwhile, hoping to inspire little Diane to become a doctor, Rainbow takes her to work at the hospital... on what turns out to be the worst day ever.
When Dre agrees to take over Rainbow’s “mom” duties for a week, the overwhelming praise he gets from everyone at his kids’ school goes to his head. He soon finds himself pushing the envelope to outdo everyone, even the school’s “crazy mom”.
Although Dre and Rainbow agreed they would no longer spank their kids, all bets might be off when Jack disobeys. Now, Zoey, Junior, Diane and a nervous Jack are afraid that their parents will go back on their word.
Dre fears his holiday fun will be ruined when the older kids balk at the glorious Johnson Halloween tradition of seeing who can pull the most outlandish pranks on each other.
After the kids turn their collective noses up at Dre's favorite cheap restaurant in his old 'hood, he decides it's time to give them a reality check. He insists all of them get jobs. But when Andre Jr. and Zoey start working at his office, he can't help but interfere, and Jack and Diane's efforts to make some spare cash leave the neighbors thinking the family has fallen on hard times, much to Bow's embarrassment.
Dre’s mother, Ruby, comes for a visit, and she smothers her pork chops with gravy, Dre with love, and would like to flat out smother Bow, who feels the same way about her. Dre tries to find a way to get the two most important women in his life to get along.
Dre wants the family to feel more connected so he encourages "Team Johnson" to embrace what it means to have each other's backs. But Dre creates trouble for himself when he falls short of Bow's expectations. Meanwhile, Bow and Dre invoke "Team Johnson" and put the less-than-enthusiastic Zoey and Andre Jr. in charge of babysitting the twins
Dre campaigns to be the new Santa at the annual office Christmas party, but when that honor goes to Angelica, the lovely head of HR, he goes to great lengths to unseat her, because he's convinced Stevens & Lido needs a black Santa. Meanwhile, Bow is tired of competing with Ruby over who cooks the big Christmas Eve dinner.
Dre thinks Rainbow is questioning his machismo after another man dismisses him in front of her. But when Pops swoops in to help his son save face, Ruby is attracted to this show of manliness and the couple reignite their love affair. Meanwhile, things get awkward when Jr. is selected to play "Romeo" to his sister Zoey's "Juliet" in their school play.
On the way to the Johnson family's annual MLK holiday ski trip, Dre realizes his children may not know the significance of Dr. Martin Luther King, Jr. so he decides to inundate them with Dr. King history facts. Once they arrive at the ski lodge, Dre finds a unique way to prepare Junior for a real world that includes intolerance.
Although Dre and Rainbow find they always end up quarreling on their annual Valentine's Day date, this time around, Dre is determined to do everything right and keep the peace. Meanwhile, Diane realizes she may not have received many Valentine's cards because she is too critical, so her siblings decide to teach her how to give a compliment
When Zoey brings home her first "serious" boyfriend, a boy from school also named Andre, Dre takes an instant dislike to him for many reasons, including the fact that he's white, from France and rather worldly for a kid. He's thrilled when they break up...until he learns that Andre dumped Zoey because she's too shallow, something Dre takes as a personal affront.
Dre schools Andre Jr. in the art of "playing the dozens," trash talking someone into submission, after he's intimidated by a bully at school, but he succeeds a little too well with his plan; Bow struggles with sleep deprivation when Diane develops a fear of the dark.
Dre, determined to make up for the no-frills, last-minute wedding he and Bow had, organizes an amazing vow renewal for their 15th anniversary. But when Bow's hippie-dippy parents, Alicia and the very white Paul show up unannounced -- bombshells are dropped and old disagreements re-ignite between the two families, especially with Pops and Ruby.
Things begin to fall apart, in more ways than one, when Dre hurts himself playing basketball right before his 40th birthday. He hands the planning of his big party over to his much younger, hipper assistant, fearing he really is getting too old to be cool. Bow and Ruby face off over who can get Dre the best gift, and the kids try to figure out what to give their dad for his special day.
Bow learns from her colleague that Dre never had the vasectomy a few years back that he was supposedly scheduled, so she decides to see if he'll come clean and tell the truth.
When Bow reconnects with her college friends on Facebook, she invites them over for an elaborate dinner party and tries to impress them. But the night of the party, Dre ends up learning a lot of new information about Bow's past. Meanwhile, the kids discover that one of Bow's friend's was on "The Real World," so they decide to shoot their own reality show and document the party.
When super cool — and white – exec Jay Sloane challenges Dre over his street cred and picks inept Charlie for a big urban market account, Dre finds himself questioning his “blackness.” Pops gets a letter from the IRS and fears the worst.
When teenager Zoey goes through a mini-rebellion phase by pushing boundaries and acting out, Dre wants to lay down the law, while Bow insists on a softer approach like her mom did with her.
Dre's sister, Rhonda, is in town for Mother's Day and although she hasn't come out to the family, everyone knows she's gay - except Ruby -- and Bow thinks Dre should tell her the truth. Meanwhile, Zoey tries to help Junior have better 'gaydar,' and Diane and Jack compete to see who will have the perfect Mother's Day gift.
Liberals Dre and Bow go ballistic when Junior declares he's joined the Young Republican Club to impress a girl (ironically named Hillary). Since they really can't believe any reasonable black people would be Republicans, Dre and Bow arrange to meet Hillary's wealthy and conservative parents. Meanwhile, everyone teases Zoey when she finds out she needs glasses.
Jack and Diane look for clues about their roots for their class assignment, a history of the Johnson family. But when they can't find anything out about the family's past, Pops comes to the rescue with the colorful story of how "Pops' Pops' Pops'" great-great grandfather, Drex Johnson, bet the future of the Johnson family against a ruthless gangster, Elroy Savoy, during the 1920s Harlem Renaissance